


Lessons From Gabe

by fanfic814



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Fluff and Smut, Hand Jobs, I Can't Believe I Wrote This, I should apologize, M/M, Plot What Plot/Porn Without Plot, Porn with Feelings, Sex, Shameless Smut
Language: English
Status: Completed
Published: 2015-07-23
Updated: 2015-07-23
Packaged: 2018-04-10 19:48:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,909
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4405160
Author URL: https://archiveofourown.org/users/fanfic814/pseuds/fanfic814
Summary: <blockquote class="userstuff">
              <p>Cas doesn't want to seem inexperienced... Gabriel to the rescue!</p>
            </blockquote>





	Lessons From Gabe

"How are things with you and Dean, little brother?" Gabriel asked, bringing Cas a slice of fluffy white cake and a steaming mug of coffee.

Castiel set his treat on the coffee table and sighed. "Same as always," he started, feeling his face flush. "He makes me so crazy, Gabe. He's always eye-sexing me and touching me and flirting..."

"Touching you where?" Gabriel asked, swallowing a mouthful of cake.

"Not like that. I mean... he's just kind of handsy. Always touching my shoulder or grabbing my arm, or ruffling my hair... stuff like that. Maybe I'm just imagining it," Cas sighed.

"I wish I had some good advice for you, Cas. The man is head over heels for you. He's just in denial. Some weird fear about his sexuality apparently. I'll never understand why humans are so hung up on that sort of thing."

"How do you know? Maybe I'm making something out of nothing, Gabe."

"Cassie, sweetheart, trust me."

"But...

"Alright, alright. Sam already spilled the beans," he winked. "Pry it outta me already!"

"Oh!" Cas felt his face reddening again, but he couldn't hide his grin if he tried.

"Just keep pushing him. You'll be in his pants in no time," Gabe teased.

"Gabe!"

"C'mon, tell me you're not anxious to sex Dean Winchester!" Gabe challenged, grinning.

"Well I... I am anxious, but not exactly the way you think," Cas stammered. He shoveled a big bite of cake into his mouth.

Gabriel cocked his head and narrowed his eyes curiously. "You scared? What are you worried about?"

"Because I don't know what I'm doing! I have no idea how to please an angel nevertheless a human, Gabe!" Cas clamped a hand over his mouth at his spontaneous confession.

"Wait, Cassie, you're not telling me you've never...?"

Cas sighed and covered his face. "Please don't laugh."

"I'm not gonna laugh, I just don't understand how it could happen! You're a catch, Cas. I thought for sure you'd at least slept with Hannah. Though granted, things are different with a male."

"I told you, Gabe. Our relationship was completely platonic. She wanted it to be more, and when she started getting more aggressive about it, I kind of told her we couldn't hang out anymore."

"Huh," Gabriel pondered. "So you've never had sex. What about... other stuff?"

Cas bowed his head, embarrassed.

"Aw, Cas. It's okay. You'll be fine, really. When the time comes, you'll figure it out. Just let him lead and do what feels good."

Cas huffed. " But what if I want to do stuff to him? And I just... I don't want to make a fool of myself. Gabe, you know what you're doing. Maybe you can teach me?" he begged.

"Hmm. I suppose I could give you a few pointers," Gabe said. "But really, it's hard to talk you through it. It's kind of something you just have to do."

"So... show me," Cas begged. "I really don't want to seem so inexperienced. Please, Gabe?"

Gabriel paused, "Are you asking what I think you're asking me, Cassie? Not that I'm not into it, because I am. I just don't know how to respond..."

Cas nodded. "Would... would Sam be okay with it?"

"Sam and I have an open relationship, Cas. He's fine. Besides, you're my brother. I don't think this counts anyway. I'm just trying to make sure you're okay with it."

"Gabe, I trust you. And I'd rather learn with someone I know. So you'll teach me?" Cas asked again.

Gabe shrugged. "Sure. Sure, I can teach you whatever you want to know, Cas. Let's go up to the bedroom. It'll be comfier there."

Cas knew Gabriel was quite versed in sex with humans and he was rather confident in his abilities. He also had no qualms about casual sex, so he figured Gabe wouldn't make a big deal about it. And sure enough, Gabe had barely even hesitated. Cas had accidentally popped in on Gabe and Sam having sex once - If Sam's pleasured moaning was any indication, Gabe was certainly the right person to ask.

"Okay, Cas. First things first. Eye contact. I know you and Dean are both pros at this one with the looks you shoot each other. Nothing like a good eye-fucking throughout the entire process. Now. I guess we should start with a kiss. Seems like a good place to begin. Pretend I'm Dean. Hit me with your best shot."

"Um..." Cas hesitated. "I don't know if I can..."

"Fine, fine. I'll get us started." Gabriel tilted his head up towards Cas and used his hands to pull him down to his level. He pressed their lips together firmly and gave him a few nibbling kisses. "Now," he said in between, "you probably want to... go for a little tongue action." He gently worked Cas's lips apart with his own, letting just the slightest bit of tongue tease along Cas's. Cas eagerly emulated what Gabe had done, and Gabe responded with an enthusiastic grunt. Gabe let his tongue caress deeper and Cas moaned this time, just before pressing his own tongue further into Gabe's mouth. "Yeah, like that," he mumbled. "Just don't be so stiff. Let your hands roam a little..." Gabe smiled as he broke their kiss, "Good, Cas! You're a natural. See how you don't want to just cram your tongue down their throat? Much nicer if you use a little finesse."

Cas nodded breathlessly.

"Now depending on your situation, you can either tear clothes off or tease them off. If you're in that desperate want-need-right-now mode, you might just want to tear clothes off with reckless abandon. Otherwise, it's nice to remove clothes slowly, teasingly. Watch." He unknotted Cas's tie and pulled one side slowly. "And eye contact here," he added, letting the tie drop at his feet. Then he started to unbutton Cas's white dress shirt, leisurely working his way down the buttons, dragging his finger down the newly exposed skin as he went. "You might also want to change it up with some kisses," he said, pressing a few small kisses to Cas's collarbone. Cas shivered. When he had the shirt completely unbuttoned, he ran his hands over Cas's shoulders and down his arms, letting it fall to the floor. "Nice, right? More romantic I guess. Not that ripping buttons and tearing clothes isn't great too..."

Cas nodded. "I have goosebumps."

Gabe smiled. "Now your turn."

Cas reached for Gabe's buttons with shaky hands and slowly, slowly started unbuttoning. Gabe watched him with unflinching eyes. Cas slid his hands down Gabe's chest before pulling the shirt off his shoulders.

"Good," Gabe praised. "Now do the same with the pants."

Cas managed to get both of their pants off rather quickly.

"We'll leave these on for now," he said, pulling at the waistband of Cas's boxers. "Lay down." Cas did. "Now I know you probably want to jump right into the cock stuff, but don't forget there are other sensitive parts." He ran a finger around Cas's right nipple, teasing it with his fingers to a stiff peak as Cas moaned. Then he lathed over it with his tongue a few times, and Cas cried out.

"Oh! Oh Gabe. I never even thought to touch there," he panted.

Gabe grinned. "Touch everywhere, Cas. And don't just use your hands, use your mouth too. Explore your own body. You'd be surprised what feels good with the right touch." He ever-so-lightly dragged a fingertip across Cas's inner elbow, giving Cas goosebumps. He nibbled gently at his collarbone again and then kissed the spot between his neck and shoulder that made him shivery. He nudged behind his ear and tugged at his earlobe with his teeth. He kissed the sensitive dip in his hipbones and slid his tongue gently up his inner thigh.

"Yes," Cas hissed. "So many places I haven't explored..."

"Mmmhmm. Sometimes it's nice to tease a little. Don't just go straight for the goods. There's much to be said for a quick and dirty fuck too, of course, but I'm guessing since you're new to this might want to slow down and enjoy it."

Cas nodded.

"Okay," Gabriel continued. "Moving on." He reached down and fondled Cas through his boxers, causing Cas to yelp in surprise. "You're already nice and hard, so that's good. Let's take these off and do something about it, huh?"

"Y...yes," Cas squeaked.

Gabriel slowly slid his boxers down, nuzzling against his thigh as he went. "Wow, Cassie. You sure know how to pick a vessel. Jimmy was a good choice."

Cas flushed. "Why do you say that?"

"First of all, you're fuckin' gorgeous, of course. But Hell-o! You're also hung, Castiel!"

"I don't understand?"

"You're uh... very well endowed," Gabriel said.

"Is that desirable?"

Gabe threw back his head and laughed. "It is to me. But seriously, this is nice," he said, inspecting it as he palmed it in his fist. "Bigger than average but not too huge, nice thickness... Man, what I wouldn't give to see you fuck the smirk off Dean Winchester's face with this thing." He pumped his fist a few times and Cas jolted immediately. "Feel good?" Gabe asked.

"Ohhhh... yes," Cas moaned.

"Good. You're such a good student, Castiel. So eager to learn. So... if you're going to be doing this for any extended period of time, you're going to need some lubrication. You don't want to rub the damn thing raw. You can just spit in your palm if you like, but let's do it up right, shall we?" Gabe snapped his fingers and a bottle of cherry-scented lube appeared in his hand. "This is lube. It'll make things good and slippery." Gabe poured a little into his palm and continued stroking.

Cas gasped, "Oh! Yes. That's nicer. This is... very pleasurable, Gabriel."

"Yeah. You can do this yourself too you know. A little lube and some quiet time... good practice."

"Yes," Cas groaned. "I think I'm going to need a lot of practice..."

Gabe grinned. "Mmmhmm. You can take this bottle home with you, Cassie. Fuck, I'm a horrible teacher. This is making me horny as hell."

"That's... that's good if you're going to show me things, isn't it?" Cas moaned loudly and squirmed on the bed.

"Yes and no. I'm supposed to be instructing you, not fucking you senseless." He took a deep breath and looked at Cas's face. "Oh shit, you're getting close already aren't you?"

"C...Close to what?" Cas panted. "Oh god, Gabe. It feels really good!"

"Shhh... Okay, Cassie. We've gotta slow down for a minute."

"Why?" Castiel cried.

"Because there's so much more to learn!" Gabriel removed his hand as Cas whined.

"No, please!" Cas begged.

"Oh sweetheart, I'm not going to leave you hanging," Gabe said, chuckling softly. "We're just going to move on to something else. Blowjobs." Gabriel immediately slid Cas' dick into his mouth. "See?" he mumbled, "Pretty good, right? You don't wanna just suck, you want to tease with your tongue a little too" He pulled back and licked a long stripe up the shaft, curling his lips around the tip and bobbed his head a few times, before pulling back and swirling his tongue around the head. He placed two strong hands on Cas's hips to calm him. "Oh, don't thrust if you can help it. Humans have this thing called a gag reflex and you don't want to choke them."

"Gabe! I feel weird," Cas exclaimed. "Oh fuck," he whimpered.

"It's okay, Cas," Gabriel said softly, pulling back to stroke him again with his hand. "That's supposed to happen. It gonna feel really amazing in a minute." Gabe continued stroking him while swirling his tongue around the tip. He used his spare hand to fondle Cas's balls which were firm and tight against his body now.

"Not long now," he whispered. "Just relax." He slid up lay alongside Cas as he stroked and Cas gripped onto him desperately as the tiny tremors began to rip through him.

"Gaaaaabe," Cas moaned.

"Shh, you're okay," Gabe whispered.

Cas grabbed him and pulled him closer, mashing their mouths together in a kiss before he started moaning loudly into Gabriel's open mouth. Gabe just looked down and smiled at him. "Doin' good, Cassie. So good for me, sweetheart."

Cas shrieked in panic as he began to come, and Gabriel pushed their mouths together again, kissing away the little moans and cries as best he could. "You okay?" he asked, finally pulling away as Cas started to come down.

Cas nodded slowly, still panting. "That was... that was really good."

Gabe grinned. "That was just the appetizer, Cas. Just wait 'til the main course." Gabe touched a finger to him and the mess disappeared. He put an arm around Cas's waist and snuggled into his shoulder, pressing a few tiny kisses to his chest.

Cas laughed weakly. "I'm not sure I can handle the main course."

"Oh you can. Give it a few minutes and you'll see. Another benefit of being an angel - we don't have to wait long to get it up again. Humans, it sometimes takes them a while, so you'll have to be patient. Frustrating things, humans. Of course, if you're feeling particularly naughty, you can help them along with your grace..."

Cas flushed. "You do not do that to poor Sam," he laughed.

"Oh, but I do! He loves it. My sweet moose is quite insatiable. He'll fuck until he's too sore to move. You know, Sam and I are into group stuff if you can talk Dean into it someday..."

"I don't think Dean is going to want to do stuff with his brother," Cas laughed.

"Oh Cas, I guarantee they've fooled around before. Anyway, just something to keep in mind... You're probably good by now, huh? What do you think? Top? Bottom? I'm good either way."

"Top or bottom what?"

Gabe laughed. "Do you want to be the fuck-er or the fuck-ee?"

"Oh," Cas stuttered. "I.. I don't know. Um..."

"Just a guess, but since Dean's been in denial so long, I'd assume it's gonna take some coaxing before he'll let you go to town on him. I'd peg him as a top, personally. Does that make it any easier?"

Cas nodded. "Is it going to hurt?"

"A little. Nothing you can't handle, Cassie. It's not painful, just... a little uncomfortable until you get used to it. And then it gets really good. I'll warm you up really well first. If I'm doing anything you don't like, tell me to stop, okay? Don't worry, I'll try not to get too kinky."

"Kinky?" Cas asked curiously.

"Oh you know, like spanking, tying you up, eating out your ass, kissing the cum back into your mouth... I'll try to refrain from that sort of thing. Unless you ask me to," He said with a smirk.

Cas felt himself turning bright red. He forgot just how experienced Gabriel was. He didn't want to admit some of that sounded pretty interesting. He remembered spanking from the one time he stumbled upon porn and he'd liked it a little too much. Perhaps he could get Gabe to go over some of that with him another time.

Gabriel stood up and slid his boxers off and lay down next to Cas, lazily stroking his cock in his left hand, reaching over to stroke Cas with his right. Cas sighed happily and rocked into his touch. "Mmm, you've loosened up so nicely, Cas. You were so stiff and anxious when we started," Gabe cooed.

Cas nodded. "I was nervous at first. But I realize that was silly. I trust you, Gabe."

Gabe grinned and slid on top of him. "Thank you, Cassie." He nuzzled Cas's cheek, making him giggle. "So this," he said, moving his hips so that their cocks gently rubbed together, "can be fun with or without clothes." He leaned in and nibbled at Cas's neck while he worked.

Cas gasped. The feeling of skin-on-skin and the weight of Gabriel pressed against his body left him swooning a little. This was a feeling he could definitely get used to. "Mmm. Yes, this is nice," he agreed.

Gabe smiled and continued on for a few minutes, letting Cas rub up against him, then gently pushed himself up, sliding down Cas's body, kissing a trail down his chest and stomach. Cas arched his hips at the end, and Gabe caught the tip of his dick in his mouth, sucking it and letting it go with an audible 'pop'. Gabe realized he was enjoying watching Cas become all loose and pliant for him just a little too much, but he couldn't find it in him to care at the moment.

"Okay, bend your knees for me a little." He knelt between Cas's legs and positioned them where he wanted them, then grabbed at Cas's cheeks and spread them a little more. "Fuck, this is a hell of a view, Cassie."

Cas was squirming with need already. "Please, Gabe,"

"Alright, alright, sweetheart. I'm gonna open you up with my fingers first, okay? Now, no matter what you're putting up there, you're gonna want a lot of lube..."

"Hurry," Cas panted.

"I'm trying to teach you something, Cas!" Gabe laughed. He moved to lay at Cas's side and slicked up his fingers, then reached between his legs. "Now just relax into it. Don't tense up." Cas hissed as the first finger slid inside him. "You okay?" Gabriel asked.

Cas nodded. "Feels... strange."

Gabe laughed. "Oh good, that's what I was going for. 'Strange'," he rolled his eyes playfully. "How's this?" He curled his finger and rubbed at a little spot that made Cas shriek.

"Ohmygod what was that?" Cas panted.

"You like?" Gabe teased, doing it again.

Cas let out a loud whimper. "Yes, yes! Do it again."

"Patience, Cassie. Don't wanna blow your load before we even get started, do you? Can you take another one for me?"

"Another?"

"Mmmhmm. Gonna get three in there eventually. I need you good and stretched to take my cock, sweetheart."

Cas moaned and nodded, and Gabe pressed a second finger to his hole and pressed, inching it slowly inside as Cas groaned. "Okay," he gasped. "That one hurts a little."

"Just wait it out a minute. Try to relax. I can feel you clenching."

Cas gritted his teeth and took a deep breath. "I...I think I'm okay now."

"Good boy," Gabe praised, rewarding him with a little rub against his prostate before working his fingers to stretch him.

"Fuck!" Cas yelled. "Gabe, I need more!" Cas was thrusting now, trying hard to fuck himself onto Gabe's fingers but Gabe wasn't about to let him finish himself off just yet.

"Almost there, sweetheart. Can you take one more for me yet?"

"Yes, just... do it!" Cas gasped.

"Bossy, bossy, Castiel. If I hadn't just promised to behave myself, I'd be spanking you," Gabe teased.

"Yessss," Cas gasped.

"Like that, do you?" he grinned. "Let's just get you through the basics first, eh?" He pressed the third finger against him and Cas cried out. "You're okay sweetheart. You're okay," Gabe whispered, kissing his chest. Cas gripped him tightly and yelled again as Gabe inched in slowly. "Tell me if you want me to stop, Cas," Gabe reminded. Cas shook his head 'no', but his breath was coming in short sobs now. Gabe quickly slid the rest in and paused as Cas groaned. "I know, Cassie. It'll be okay in a minute," he whispered. "Deep breath."

Cas sat still for a few minutes just panting. When Gabriel finally felt him start to relax, he rewarded him again with a little caress to that spot that made him shiver and moan in pleasure.

"Fuuuck," Cas moaned. "I'm good now. Gabe, please..."

"Okay, Cas, okay." Gabe pulled his fingers out and Cas nearly growled at the sudden loss of pressure. Gabriel quickly lubed himself up and pushed into Cas in one quick thrust. Cas's head went back and his hips arched forward as he yelled.

"Yessss, ohmygod, Gabe. Thankyouthankyou," Cas blubbered..

"Shhhh," Gabe laughed. "I guess you're doing okay then?"

"Mmmhmm," Cas mumbled, pulling Gabe down for a kiss. Gabe kissed him back softly for a few minutes, then chuckled and gave a short, sharp thrust, causing Cas pull back moaning.

"You like that, sweetheart?" Gabe teased, thrusting hard again and making Cas yelp. Cas was already coming apart, so he slowed down, thrusting lazily. "How does it feel, Cas?"

"So good, Gabe. Better than anything I've ever felt. Hot and full and tight and a little sore... and when you hit that spot... I see stars. Literally. I feel like I'm going to pass out it feels so good," Cas was babbling excitedly.

Gabe smiled. "Ohh, Cassie. I think you were worried for nothing. Told ya you're gonna be just fine." Gabe assured him.

Cas giggled, and began nibbling at Gabe's shoulder. "Mmm. I think I'll be okay. This is nice though. I'm glad we did this. You're so good to me, Gabe."

"Yeah. We should have done this a long time ago," Gabe agreed, punctuating his statement with a few sharp thrusts, making Cas tremble. "Hey Cas, I'm gonna flip us, ok? Let you be on top for a bit," he grinned. Cas nodded enthusiastically. With a careful roll, their spots were suddenly reversed.

"Ohhh Gabe," Cas whined, "It feels deeper this way."

"Push up on your knees, Cas. Don't hurt yourself. You can raise or lower yourself however you want," Gabe instructed.

Cas found an awkward rhythm, thrusting against him and they both moaned simultaneously.

"That's it sweetheart," Gabe urged. "Fuck, you're so tight. God you're beautiful, Castiel. And you look so damn good riding my cock." Cas's dick bounced against his stomach with every downward thrust, and Gabe reached up to stroke him.

Cas nearly doubled over at the touch. "Oh! Gabe! I'm close. So close!" he groaned.

"Me too, Cas," Gabe gasped. "Can I come in you or should I pull out?" he asked frantically.

"Stay," Cas rasped. Gabe nodded and started thrusting upwards while he simultaneously sped up his strokes.

"Gabriel," Cas whimpered just before his climax tore through him.

"Yeah, Cassie. Fuck," Gabriel yelled as he thrust harder, watching Castiel come apart on top of him. Gabe groaned in blissful agony as he spilled into him, watching Cas shoot his shuddering release over his chest.

Cas collapsed on top of Gabe, feeling sated but worn out. He caressed Gabe's face with both hands and frantically kissed as Gabe wrapped his arms around him.

"You okay?" Gabe asked softly, ruffling his hair.

"Mmmhmm," Cas mumbled tiredly. "So good."

"Feel any better about the whole thing?"

"Yeah. I'll be fine now."

"Good," Gabriel teased, "Now go forth and be fucked senseless by Dean Winchester."

Cas giggled. "I'm exhausted."

Gabe gently snapped his fingers and cleaned them up. "Why don't you try to sleep, Cas?"

"Why would I do that?" Cas mumbled.

"Because you look utterly fucked-out. Close your eyes and relax, sweetheart. Just because you don't have to doesn't mean you can't."

Cas nodded. "I love you, Gabe. Thank you," he sighed happily.

"I love you too, Cassie."

"Gabe...?" Cas yawned.

"Yeah?"

"Can I practice what I learned on you later?   And maybe you can teach me about the spanking..."   
  
Gabe laughed and swatted at his ass. "That's my boy."


End file.
